(2R,3R)-1-(Benzyloxy)-4-(phenylthio)-2,3-butanediol | 151359-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-1-(Benzyloxy)-4-(phenylthio)-2,3-butanediol
• 英文别名: (2R,3R)-1-phenylmethoxy-4-phenylsulfanylbutane-2,3-diol
• CAS: 151359-21-6
• 化学式: C₁₇H₂₀O₃S
• 分子量: 304.41
• InChiKey: OCVOQEIDWMANBG-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R)-1-(Benzyloxy)-4-(phenylthio)-2,3-butanediol 在 吡啶 作用下， 反应 1.0h， 生成 (2R,3R)-1-(Benzyloxy)-4-(phenylthio)butane-2,3-diol diacetate
  参考文献：
  名称：

  An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction

  摘要：

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.

  DOI：

  10.1021/jo00088a045
• 作为产物：
  描述：

  (E)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-2-butene 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 AD-mix-β 作用下， 生成 (2R,3R)-1-(Benzyloxy)-4-(phenylthio)-2,3-butanediol
  参考文献：
  名称：

  Synthesis of carbohydrates and related polyhydroxylated compounds employing asymmetric dihydroxylation. 1. An access to erythro-diols

  摘要：

  Asymmetric dihydroxylation provides an easy access to tetrose: threose directly from the (E)-olefin 1, and erythrose via an irreversible Payne-type rearrangement - opening process of the threitol cyclic sulfate 5.

  DOI：

  10.1016/s0040-4039(00)60654-8

文献信息

• Stereospecific ring-opening reaction of epoxy sulfides with phenylboronic acid via episulfonium ions
  作者：Hiroyuki Hayakawa、Naoko Okada、Masaaki Miyashita

  DOI：10.1016/s0040-4039(99)00412-8

  日期：1999.4

  The ring-opening reaction of epoxy sulfides with phenylboronic acid in benzene has been demonstrated to occur stereospecifically via episulfonium ions, i.e., with double inversion of configuration, giving rise to phenylboronic esters of 2,3-diols in quantitative yields.

  已证明环氧硫化物与苯中的苯基硼酸的开环反应是通过ulf磺酸盐立体定向发生的，即，具有两次构型反转，以定量收率产生了2,3-二醇的苯基硼酸酯。
• Ko Soo Y., Malik Majbeen, Dickinson A. Frances, J. Org. Chem, 59 (1994) N 9, S 2570-2576
  作者：Ko Soo Y., Malik Majbeen, Dickinson A. Frances

  DOI：——

  日期：——
• An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction
  作者：Soo Y. Ko、Majbeen Malik、A. Frances Dickinson

  DOI：10.1021/jo00088a045

  日期：1994.5

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.
• Synthesis of carbohydrates and related polyhydroxylated compounds employing asymmetric dihydroxylation. 1. An access to erythro-diols
  作者：Soo Y. Ko、Majbeen Malik

  DOI：10.1016/s0040-4039(00)60654-8

  日期：1993.9

  Asymmetric dihydroxylation provides an easy access to tetrose: threose directly from the (E)-olefin 1, and erythrose via an irreversible Payne-type rearrangement - opening process of the threitol cyclic sulfate 5.